The road to Iona Island. Bear Mountain State Park, NY. Credit: Will Geary

Day 1: Manhattan to Poughkeepsie, NY (83 miles)

Crossed over the George Washington Bridge to west side of the Hudson river. Up 9W through Nyack, Haverstraw and Bear Mountain. Took a detour in Bear Mountain State Park to check out Iona Island, a bird sanctuary with a reputation for serving as a home to bald eagles (didn’t catch any).

We rode over the Bear Mountain Bridge back to the eastern side of the Hudson. Rode up Rt. 90 through the Hudson Highlands and Beacon until finally reaching Poughkeepsie before sundown. Poughkeepsie is home to Vassar College, a small liberal arts school.

fig Crossing Bear Mountain Bridge.

Day 2: Poughkeepsie to Bennington, VT (108 miles)

Rose early for the longest day of the journey. Head up route 9 through Rhinebeck, Red Hook and Hudson. I’m always impressed with the natural beauty of the towns that scatter the Hudson River. Dipped into western Massachusetts by way of route 20, crossing through Cheshire, Adams and Williamstown. Finally crossed the Vermont border and arrived in Bennington for a beer, burger and good night’s rest.


Day 3: Bennington to Rutland, VT (56 miles)

Shortest day of the tour, and it comes at a good time. A leisurely 56 miles up Route 7 takes us through Sunderland, Manchester, Mt. Tabor and Wallingford before arriving in Rutland, VT. I was later told that Vermonters sometimes refer to this town as “Rut-Vegas”. We stayed at a pretty crappy hotel along the highway, but were fortunate to have stumbled into a hippie sandwich shop called The Yellow Deli. It was an unusual place. The entire waitstaff sported long ponytails and biblical names like Jedediah. After some research, I discovered that this particular sandwich shop has a storied past. The Yellow Deli is apparently associated with The Twelve Tribes, an “end times” Christian organization with communities worldwide. There are some articles online suggesting that the Deli may be a cash-laundering front for a religious cult. All I know is that they make a mean turkey sandwich.


Day 4: Rutland to Burlington, VT (70 miles)

A beautiful, yet at times terrifying, ride up route 7 takes us along the Green Mountain National Forest, through Middlebury and Hinesburg. Really pretty riding. There were roads, trees, and the occasional dear.

Arriving in Burlington was a fantastic feeling. It signified have ridden through nearly the entire state of Vermont (which, granted, is relatively small) and rewarded us with the beauty of Lake Champlain.


Day 5: Burlington to Montreal (105 miles)

It was surreal to be nearing the Canadian border with nothing but a bike and a couple bags. Rode up Route 2 through the Hero Islands. A magical place.

fig Hero Islands, Lake Champlain, VT.

The roads felt longer on this final day. So did the grass on the side of the road. When I started to see signs in French, I knew Quebec was close.

fig Near the Vermont - Canada border.

Crossing through the border on a bicycle was quick and painless. The border patrol didn’t seem impressed when I told him that I was coming from New York. As I neared my destination the roads transformed from rural, to suburban, to urban highways. I reached Montreal at 7pm, when it was still light out. After stumbling across the first green space I could find - which happened to be the main quad of McGill University, I pulled over and lay down. Basking in the smell of grass, surrounded by warm sunlight and French whisperings, I felt good. Like I had broken through a metaphysical layer and opened the door to a new reality. I caught a rock show that night in Parque Jean Drapeau - a nice way to celebrate and bookend my journey. Montreal is a lovely place.

fig Arcade Fire playing in Parc Jean Drapeau, Montreal.